Chris Ginnelly is Managing Partner of GTM Performance, and an independent growth advisor on ECI Partners’ Growth Specialist Panel. He led a session at a recent ECI Unlocked CRO dinner on one of the most debated topics of the evening: how to pursue and win larger enterprise deals. Here, he distils his key takeaways.
The commercial case
While CROs might not always agree on the right approach, the reason for targeting larger, enterprise-level deals is clear. Bigger deals tend to outperform over time. They typically carry better unit economics, lower churn, and the kind of reference brand weight that opens doors to the next deal.
But the more you concentrate on larger clients, often, the bumpier the ride. Forecast volatility increases, and the gap between your base and optimistic pipeline widens significantly. It creates significant internal stress – both for the CRO having more complicated Board discussions – but also to sales teams who become much more dependent on each individual deal converting.
So, there are pros and cons, but how can you make “whale hunting” work?
Theme 1: Engineer predictability, don’t wait for it
Enterprise sales tend to resist the standard funnel and processes that work in high volume sales. Timelines tend to be longer, stakeholders can change during the process, and procurement are much more likely to be involved, often at an unknown juncture, with different needs to the department who you were selling into.
Rather than focussing on the unpredictability, it’s better to reframe it as more of a choreographed dance: the sequencing of stakeholders, the framing of value, the management of internal champions, and the sales team collectively agreeing the characteristics of a winnable deal.
Murderboarding is one of the most effective tools for this. Rather than committing resources based on optimism, the revenue team stress-tests each deal aggressively before progressing it: Where is the real decision-making power? What assumptions have we (not) verified? Where does the buying logic fall apart?
When these structures are in place, it becomes easier to engineer predictability and to focus resources on the clients that are likely to convert rather than chasing the mega deals that may never land.
Theme 2: Reduce reliance on an individual belief
The second theme was more sensitive – when selling into an enterprise, forecasts are often based on a senior salesperson’s instinct on a key account. This ends up being quite high risk (tied to one person’s view) and adds volatility to forecasting.
The solution is to take the assessment out of the individual’s hands and put it into a shared process. Structured qualification frameworks help salespeople to document, throughout the process, what they really know, and then every deal is assessed against the same criteria. The difference between belief in a deal, and the evidence, can then be highlighted and discussed at pipeline reviews. To make this work there needs to be the establishment of a cultural norm that scrutiny of a deal is not a vote of no confidence in the person running it.
Stage progression needs to tie to buyer actions, not seller activity. A deal should only advance when the buyer has done something to progress it, not when the seller has. A meeting attended is not progress. A customer taking an action to move through their own buying process is. The team should be clear on the evidence of what is required to move a deal forward at an enterprise level and that should tie directly to propensity to convert, giving CROs more confidence in the numbers they’re putting forward.
Theme 3: The skills that win volume deals aren’t always the skills that win enterprise ones
CROs shifting up in customer size might presume that their best transactional salespeople will be able to easily transition into enterprise roles. They may, but closing volume deals and navigating a nine-month multi-stakeholder process are genuinely different skills. Speed and instinct are highly valuable in one; the latter requires patience, political intelligence, and the ability to sustain a champion in your service or product over the long term. Mismatched hires or promotions can slow down success, which is especially damaging given the lead times you’re looking at when shifting up in customer size.
Compensation structures also need to reflect the reality of longer cycles and higher individual deal dependency. Enterprise sales roles typically warrant a higher base-to-variable ratio. Asking someone to carry the same OTE structure across a nine-month deal cycle as they did in a high-velocity transactional role is a retention risk as much as a motivation one.
Key lessons
Pursuing enterprise deals can be the right strategic direction for many growth businesses, but it requires a deliberate investment in the right skillsets and qualification discipline. Enterprise selling will never be predictable in the way that high-volume selling can be, but the CROs responsible for doing it successfully ensure they build the systems that work with that uncertainty rather than attempting to eliminate it.
